The Chronicles Of Todd: The 2017 Kentucky Derby, Part I

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The Chronicles Of Todd: The 2017 Kentucky Derby, Part I

“This place is a shithole,” Todd yelled from the bedroom where he’d put his bag. “Who the fuck booked this place?”

Everyone scrambled around the house trying to find a place to lay their stuff to rest for the weekend. Like with any weekend away, everyone fast-walked into the house they’d rented in hopes of finding a good enough bedroom to sleep in – which essentially meant “anything that isn’t a couch.”

“Oh, this place not pretty enough for you, Todd?” John yelled from his bedroom. “Why don’t you just go back to my place that you’ve been treating as a bed and breakfast for the last week?”

“Hey, uh,” Todd began, “Why don’t you go fuck yourself?”

Trip, Ben, and Finn stood in the kitchen howling with laughter while pouring a fifth of Early Times equally into five different roadie glasses that they’d found in a cupboard. After last year, they decided to skip The Oaks and go all in on Derby day. The box they’d made their stomping grounds last year was also taken by some corporate clients so they opted for the college route and decided to fork over the $45 for infield tickets rather than break the bank pretending to be classy in another box.

Todd entered the kitchen wearing khakis and an untucked button down with the top three buttons undone. He set his hands on the table and asked which cup of bourbon was his before further asking, “So what’re we getting into tonight?”

“Alright,” Trip started, “I got us a 9:30 reservation at Jack Fry’s and—”

“Wait,” Todd interrupted. “Who the fuck makes a 9:30 reservation? I’m starving.”

Trip made a jack-off motion with his hand and claimed, “I made it the second we booked the trip and being that it’s the busiest night of the year in Louisville, you should be thankful we have a reservation at all. Classy joint, dress nice. Todd, you’re fine in what you have on.”

* * *

The five horsemen sat down in the dimly lit restaurant. With whiskey on their breath from the two bars before, they had a glaze over their eyes that screamed “trouble.” The restaurant was busier than normal given the weekend and most tables were not only full but spilling over with people standing up next to them stopping in for a drink. The waiters weaved through the patrons trying to remember which table was at which point in their meals.

Once their waiter finally came, John took it upon himself to order for the table. Squinting at the menu, he ran his finger down the wine list attempting to find something that the table would like while the waiter hovered over his shoulder doing everything but actually say, “Hurry the hell up.”

“Uhhhhhh, alright,” John yelled over the crowd. “We’re going to start with two bottles of this cab for the table and five Woodford old fashioneds.”

Before the waiter could grab the menu from him, he chimed in again with a, “And can we get some fried oysters for the table too? Thanks, bud.”

Ben remained on his phone throughout the course of the ordering until he chimed in, “Hey, I’m talking to this girl who I just matched with a few minutes ago – she wants us to meet us at their hotel after dinner. They’re staying at The Brown and said we should meet up with them.”

“Look at you,” Finn said. “Just getting into the thick of it early. Love it.” Finn and John went on to clarify that if they went, no one was to Snapchat what was happening (or at least who they were with).

Upon finishing their first round of old fashioneds, their waiter made their way back to the table and confirmed they’d like another round. Too busy to fill up their wine glasses, each of the guys gave themselves heavy pours to hold them over before the next round came.

“Yeah, uh, I’ll do the stilton salad with the filet,” Todd shouted to the waiter with one hand cupped around his mouth.

“How’d you like that done?”

“What?” Todd yelled.

“How would you like that done?” the waiter over-enunciated.

“Medium rare,” Todd clarified. “More on the rare side if possible.”

Going around the table clockwise, Trip responded, “I’ll do the exact same.”

“Same for me,” John echoed.

“Yep, me too,” Finn repeated.

“I guess I’m doing the same fuckin’ thing,” Ben screamed using his menu as a means to shield his voice from the crowd.

The waiter quickly grabbed their menus and ran off, followed up by another waiter showing up with their second round of drinks. He set them all down on the table in one group and ran off without a care.

“Real nice service we’ve got here,” Todd joked to Trip.

“Say,” Todd asked began while looking at Ben. “Where these chicks from?”

Ben glanced at the rest of the table with a smirk on his face before snarkily responding, “Unlike you, Todd, I didn’t get her whole life story.” Everyone laughed before he continued, “But from what I can tell, she went to Auburn and lives in D.C.”

“S-E-C! S-E-C! S-E-C!” Finn chanted while slamming his fists on the table. The only other person to join in was John, who had already established earlier in the night that he was going to use his Adderall buzz solely to become the best wingman possible. He let out a “War Damn Eagle!” and chugged his old fashioned down before waving his finger in the air signaling for another.

“Jesus,” Ben laughed. “You realize I’m the one trying to go home with these girls and not you, right?”

The service at the restaurant, while not desirable, lent itself to drinking as many cocktails as humanly possible while they waited for their steaks to come out. Any time you have more than a couple stiff brown drinks before dinner comes out, you know the sustenance isn’t going to do anything to you for the long haul. The wine was an unnecessary addition to an already volatile cocktail situation, and every one of the guys was showing signals of teetering on the edge of brown out while the waiter set the steaks down in front of them. Their excitement for the night was the only thing keeping them afloat, and it was no question that they’d make it to late in the night whether they remembered it or not.

Their table remained silent in the bustling restaurant while they each plowed through their steaks. Ben broke the silence echoing, “She just messaged me again – they said they’re at the hotel bar and are ready when we are. Should we just finish these drinks and Uber over there? Apparently they’re going to some strip of bars that go all night.”

“We go there last year?” Todd asked. “I honestly can’t remember.

“No clue,” John responded before turning to Ben and requesting, “Give me your phone, I want to see these broads.”

Todd drunkenly attempted to pull out his wallet dropping it on the floor before finally recovering it and putting it on the table. He took his American Express out and set it down next to his empty plate. “I’ll get this and you guys can Venmo me,” he told the table while looking for their waiter.

“I’ve got an Uber coming in ten minutes,” Ben followed up. “Only 2.5x surge pricing – wonderful.”

All the guys looked at their phones waiting for the bill to show up. Todd’s phone had been upside down all night and he flipped it over to reveal nothing but ESPN alerts, work emails, and a few messages from a different group text from the guys he was with. Squinting in an effort to see straight after opening his iMessages, he started a new message and typed “C” before scrolling down to Claire.

Typing hesitantly, he reread his message three times before sending trying to make sure there weren’t any glaring errors.

“You doing Derby again this year?”

Image via Historic Louisville

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Will deFries (Twitter / Instagram) is a Senior Writer at Grandex and the world's foremost authority on Sunday Scaries (Twitter / Instagram). Email me at

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